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Compound Detail

CHEMBL26820

(E)-ISBOGREL
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O=C(O)CCCC/C=C(\c1ccccc1)c1cccnc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL26820
Name (E)-ISBOGREL
Phase Preclinical
Structure Type MOL
InChI Key UWPBQLKEHGGKKD-GZTJUZNOSA-N
5
Targets
24
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

281.4
MW (Da)
4.16
ALogP
2
HBA
1
HBD
50.2
PSA (Ų)
0.78
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H19NO2
MW 281.36
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.20

Activity Summary

IC50 12 meas. best 9.05
Kd 11 meas. best 5.2
Ki 1 meas. best 5.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Thromboxane-A synthase
CHEMBL1835
 IC50 9.05 7.684 0.9 10
Rattus norvegicus
CHEMBL376
 IC50 6.6 6.6 250.0 1
Unchecked
CHEMBL612545
 Ki 5.57 5.57 2700.0 1
Thromboxane A2 receptor
CHEMBL3156
 Kd 5.2 5.2 6309.6 2
Thromboxane A2 receptor
CHEMBL2069
 Kd 5.09 4.945 8200.0 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Thromboxane-A synthase IC50 = 0.89 nM 9.05 In vitro inhibition of TXB2 production by incubating prostaglandin H2 with human... 11814792
Thromboxane-A synthase IC50 = 2.9 nM 8.54 Activity against TXA2 synthase in bovine platelet microsome 8496929
Thromboxane-A synthase IC50 = 17.0 nM 7.77 In vitro Inhibition of thromboxane synthase from human blood platelet microsomes 7861416
Thromboxane-A synthase IC50 = 20.0 nM 7.7 In vitro inhibitory activity against human microsomal thromboxane synthase. 7752186
Thromboxane-A synthase IC50 = 26.0 nM 7.58 Inhibition of horse thromboxane A2 synthase evaluated as molar concentration req... 1992126
Thromboxane-A synthase IC50 = 26.0 nM 7.58 Inhibitory activity against thromboxane B2 formation (TXA2 synthase) by incubati... 4038746
Thromboxane-A synthase IC50 = 48.7 nM 7.31 In vitro for inhibitory activity against thromboxane synthase 9876106
Thromboxane-A synthase IC50 = 48.7 nM 7.31 In vitro inhibition of thromboxane synthase (TSI) activity was determined by usi... 9873463
Thromboxane-A synthase IC50 = 100.0 nM 7.0 In vitro inhibition of collagen-induced thromboxane A2 production in human whole... -
Thromboxane-A synthase IC50 = 100.0 nM 7.0 In vitro TXA2 synthase antagonism through inhibition of collagen induced thrombo... -
Rattus norvegicus IC50 = 250.0 nM 6.6 In vitro inhibition of thromboxane A2 production in rat platelet-rich plasma. 2724303
Unchecked Ki = 2700.0 nM 5.57 Tested for specific binding of radioligand [3H]U-46619 to thromboxane A2 /prosta... 8496929
Thromboxane A2 receptor Kd = 6309.57 nM 5.2 In vitro thromboxane A2 receptor antagonism through inhibition of U-46619-induce... -
Thromboxane A2 receptor Kd = 6309.57 nM 5.2 In vitro thromboxane A2 receptor antagonism through inhibition of U-46619 induce... -
Thromboxane A2 receptor Kd = 8200.0 nM 5.09 In vitro for antagonistic activity against thromboxane synthase receptor 9876106
Thromboxane A2 receptor Kd = 8200.0 nM 5.09 In vitro thromboxane receptor antagonism was determined using a human platelet b... 9873463
Thromboxane A2 receptor Kd = 15848.93 nM 4.8 In vitro thromboxane A2 receptor antagonism through inhibition of U-46619-induce... -
Thromboxane A2 receptor Kd = 15848.93 nM 4.8 In vitro thromboxane A2 receptor antagonism through inhibition of U-46619 induce... -

Literature References

PubMed DOI Target Context # Activities
7861416 10.1021/jm00004a014 Thromboxane-A synthase 6
7752186 10.1021/jm00010a005 Canis familiaris 6
2724303 10.1021/jm00126a031 Rattus norvegicus 5
7752186 10.1021/jm00010a005 Rattus norvegicus 5
8496929 10.1021/jm00063a011 Rattus norvegicus 4
1992126 10.1021/jm00105a042 Polyunsaturated fatty acid 5-lipoxygenase 3
1992126 10.1021/jm00105a042 Thromboxane-A synthase 3
- 10.1016/S0960-894X(01)81051-9 Thromboxane A2 receptor 2
- 10.1016/S0960-894X(01)81050-7 Thromboxane A2 receptor 2
4038746 10.1021/jm00381a005 Rattus norvegicus 2
1992126 10.1021/jm00105a042 Rattus norvegicus 2
7752186 10.1021/jm00010a005 Thromboxane-A synthase 1
7752186 10.1021/jm00010a005 Homo sapiens 1
9876106 10.1021/jm980173n Thromboxane A2 receptor 1
9876106 10.1021/jm980173n Thromboxane-A synthase 1
8496929 10.1021/jm00063a011 Homo sapiens 1
4038746 10.1021/jm00381a005 Thromboxane-A synthase 1
8496929 10.1021/jm00063a011 Thromboxane-A synthase 1
11814792 10.1016/s0960-894x(01)00731-4 Thromboxane-A synthase 1
8496929 10.1021/jm00063a011 Unchecked 1

Data from ChEMBL 36 via Core Engine